EP1967509A4 - Method for producing primary amine compound - Google Patents

Method for producing primary amine compound

Info

Publication number
EP1967509A4
EP1967509A4 EP06843156A EP06843156A EP1967509A4 EP 1967509 A4 EP1967509 A4 EP 1967509A4 EP 06843156 A EP06843156 A EP 06843156A EP 06843156 A EP06843156 A EP 06843156A EP 1967509 A4 EP1967509 A4 EP 1967509A4
Authority
EP
European Patent Office
Prior art keywords
formula
group
primary amine
amine compound
halogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP06843156A
Other languages
German (de)
French (fr)
Other versions
EP1967509B1 (en
EP1967509A1 (en
Inventor
Hiroshi Souda
Naoyuki Takano
Shinzo Seko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of EP1967509A1 publication Critical patent/EP1967509A1/en
Publication of EP1967509A4 publication Critical patent/EP1967509A4/en
Application granted granted Critical
Publication of EP1967509B1 publication Critical patent/EP1967509B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
    • C07C211/21—Monoamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/45—Monoamines

Abstract

Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen tom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)
EP06843156A 2005-12-26 2006-12-25 Method for producing primary amine compound Not-in-force EP1967509B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005371743A JP4848762B2 (en) 2005-12-26 2005-12-26 Method for producing primary amine compound
PCT/JP2006/325752 WO2007074762A1 (en) 2005-12-26 2006-12-25 Method for producing primary amine compound

Publications (3)

Publication Number Publication Date
EP1967509A1 EP1967509A1 (en) 2008-09-10
EP1967509A4 true EP1967509A4 (en) 2009-02-25
EP1967509B1 EP1967509B1 (en) 2010-04-14

Family

ID=38217982

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06843156A Not-in-force EP1967509B1 (en) 2005-12-26 2006-12-25 Method for producing primary amine compound

Country Status (9)

Country Link
US (1) US7652170B2 (en)
EP (1) EP1967509B1 (en)
JP (1) JP4848762B2 (en)
KR (1) KR101365286B1 (en)
CN (1) CN101346345B (en)
BR (1) BRPI0620609A2 (en)
DE (1) DE602006013708D1 (en)
IL (1) IL192151A (en)
WO (1) WO2007074762A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103804108B (en) * 2012-11-15 2016-08-03 沈阳药科大学 A kind of method preparing primary amine
CN104672102A (en) * 2013-11-30 2015-06-03 沈阳药科大学 Preparation method of O-substituted hydroxylamines
CN105713151A (en) 2015-12-31 2016-06-29 江苏苏博特新材料股份有限公司 Application and preparation method of concrete superplasticizer with phosphorous acid group
CN106349079A (en) * 2016-08-29 2017-01-25 浙江大川新材料股份有限公司 Preparation method of allyl amine mixture

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA805280B (en) * 1979-08-27 1982-04-28 Du Pont Antiinflammatory 4,5-diaryl-a-polyfluoroalkyl-1h-pyrrole-2-methanols and 1-(4,5-diaryl-1h-pyrrol-2-yl)polyfluoralkanones
JPS62161765A (en) * 1986-01-09 1987-07-17 Nippon Synthetic Chem Ind Co Ltd:The Production of 1-substituted-imidazole
JP3353937B2 (en) * 1993-03-31 2002-12-09 保土谷化学工業株式会社 Method for producing chloromethyl alkyl ether
JP3937489B2 (en) * 1996-05-31 2007-06-27 住友化学株式会社 Method for producing propargylamine compound
JP2002212148A (en) * 2001-01-17 2002-07-31 Koei Chem Co Ltd Method for producing monoallylamine
TWI344958B (en) * 2004-06-17 2011-07-11 Sumitomo Chemical Co Process for preparing thiazole compound
JP4839660B2 (en) 2005-04-07 2011-12-21 住友化学株式会社 Method for producing thiazole compound

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BLAZEVIC N ET AL: "Hexamethylenetetramine, A Versatile Reagents in Organic Synthesis", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE, 1 January 1979 (1979-01-01), pages 161 - 176, XP003020260, ISSN: 0039-7881 *
M. SALJOUGHIAN ET AL: "Specific labelling of putrscine dihydrochloride by heterogeneous hydrogenation with deuterium or tritium gas in dimethyl sulfoxide", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 25, 1988, GBJOHN WILEY, CHICHESTER, pages 313 - 328, XP002509761 *
S. BRANDANGE ET AL: "A convenient route to 3-pyrroline utilizing the delepine reaction", SYNTHESIS., no. 4, 1988, DEGEORG THIEME VERLAG, STUTTGART., pages 347 - 348, XP002509760 *
See also references of WO2007074762A1 *

Also Published As

Publication number Publication date
US20090287023A1 (en) 2009-11-19
IL192151A0 (en) 2008-12-29
WO2007074762A1 (en) 2007-07-05
CN101346345A (en) 2009-01-14
KR20080078696A (en) 2008-08-27
JP2007169239A (en) 2007-07-05
IL192151A (en) 2012-08-30
CN101346345B (en) 2012-06-20
US7652170B2 (en) 2010-01-26
EP1967509B1 (en) 2010-04-14
JP4848762B2 (en) 2011-12-28
BRPI0620609A2 (en) 2011-11-16
KR101365286B1 (en) 2014-02-19
EP1967509A1 (en) 2008-09-10
DE602006013708D1 (en) 2010-05-27

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